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Top USA Sailing Trips

375 Results
Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and …More

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and...

2 hours Free Cancellation
4.8 (175)
from
$60
Tiki Pub Amazing Dolphin Eco Adventure

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and …More

Likely to Sell Out
Likely to Sell Out
Fort Myers, USA

Join us for an Environmentalist led Adventure! Go to Sandbars and Beaches to see our shallow water inhabitants, cruise the bay for Dolphins, Manatee, and...

1 hour 30 minutes Free Cancellation
4.9 (10)
from
$60
Hilton Hawaiian Village Adventure Sail on the Spirit of Aloha

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet. …More

Oahu, USA

This cruise is exceptionally family-friendly, with no snorkeling or in-water activities, making it ideal for guests who want to experience the ocean without getting wet....

1 hour Free Cancellation
5.0 (3)
from
$60
Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are …More

Seattle, USA

This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are...

2 hours Free Cancellation
4.9 (218)
from
$60
Waikiki Friday Night Fireworks Cruise NYE SPECIAL CRUISE!

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring …More

Oahu, USA

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring...

1 hour Free Cancellation
4.7 (30)
from
$60
New York City Sailboat Day Cruise to the Statue of Liberty

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Experience New York by water aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as...

1 hour 45 minutes Free Cancellation
4.9 (174)
from
$60
New York Day Sail to the Statue of Liberty on Schooner America

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable, …More

Likely to Sell Out
Likely to Sell Out
New York City, USA

Offering a premium sailing experience, the Schooner America is a tribute to the original America that won the America's Cup in 1851. This classic sailboat is comfortable,...

1 hour 45 minutes Free Cancellation
4.9 (64)
from
$60
Newport Afternoon Sightseeing Sail on Classic Sailboat

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail, …More

Newport, USA

Sail on a classic sailboat in Newport, RI, and enjoy a sightseeing sailing experience around Narragansett Bay. Pass by many iconic sights during the sail,...

1 hour 30 minutes
4.9 (196)
from
$61
Newport Sightseeing Day Sailing Experience on Schooner Adirondack

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, …More

Newport, USA

See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges,...

1 hour 30 minutes
4.9 (159)
from
$61
Morning Mimosa Sightseeing Sail on Schooner Madeleine in Newport

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and …More

Newport, USA

Start your day with a morning sightseeing sail around Newport on a classic sailboat. Sailing aboard Schooner Madeleine is a great experience for friends and...

1 hour 30 minutes
4.8 (58)
from
$61
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic …More

Oahu, USA

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic...

1 hour 30 minutes Free Cancellation
4.9 (217)
from
$62
Buccaneer Pirate Cruise in Destin

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger …More

Likely to Sell Out
Likely to Sell Out
Destin, USA

Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger...

90 to 120 minutes Free Cancellation
4.8 (146)
from
$62
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the …More

Mount Pleasant, USA

Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the...

2 hours Free Cancellation
4.9 (101)
from
$63
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, …More

Mount Pleasant, USA

Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran,...

2 hours Free Cancellation
5.0 (11)
from
$63
Windjammer Classic Day Sail from Camden, Maine

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations …More

Camden, USA

See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations...

2 hours Free Cancellation
4.8 (461)
from
$65
Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s …More

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail on Boothbay Harbor’s...

2 hours Free Cancellation
4.5 (41)
from
$65
Suncoast Sailing's Day Sailing Experience!

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just …More

St Petersburg, USA

Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just...

2 hours 30 minutes Free Cancellation
4.9 (118)
from
$65
San Francisco Bay Sailing Cruise

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from …More

Likely to Sell Out
Likely to Sell Out
San Francisco, USA

Experience the beauty of San Francisco during a 1.5-hour catamaran cruise over San Francisco Bay. Sail away from bustling city and enjoy photo ops from...

1 hour 30 minutes Free Cancellation
4.9 (659)
from
$65
Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Baltimore, USA

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes Free Cancellation
4.7 (118)
from
$65
Catamaran Sailing Cruise in Monterey

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind …More

Monterey & Carmel, USA

Enjoy sailing the Monterey Bay without engine noise. You will be offered a complimentary beverage after your captain hoists the sails and catches the wind...

1 hour 15 minutes Free Cancellation
4.8 (44)
from
$65

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